Stereochemistry of the verbenols

Abstract

Nuclear magnetic resonance and chemical evidence shows that the product of lithium aluminium hydride reduction of verbenone is cis-verbenol, and that of lead tetra-acetate oxidation of α-pinene is trans-verbenol. The physical properties of both alcohols differ from those reported for the alcohols separated from the product of Meerwein–Ponndorf–Verley reduction of verbenone.